Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H14O4.2Na |
Molecular Weight | 232.1846 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].[O-]C(=O)CCCCCCCC([O-])=O
InChI
InChIKey=QFYNUCAKHMSPCY-UHFFFAOYSA-L
InChI=1S/C9H16O4.2Na/c10-8(11)6-4-2-1-3-5-7-9(12)13;;/h1-7H2,(H,10,11)(H,12,13);;/q;2*+1/p-2
Molecular Formula | C9H14O4 |
Molecular Weight | 186.2051 |
Charge | -2 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=2114832
https://www.ncbi.nlm.nih.gov/pubmed/18803456
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=2114832
https://www.ncbi.nlm.nih.gov/pubmed/18803456
Azelaic acid, a naturally occurring saturated dicarboxylic acid found in wheat, rye, and barley, possesses antimicrobial activity, affects keratin production, and reduces inflammation. One of the brand name for azelaic acid is FINACEA,Gel, 15% is indicated for topical treatment of the inflammatory papules and pustules of mild to moderate rosacea. Although some reduction of erythema, which was present in patients with papules, and pustules of rosacea occurred in clinical studies, efficacy for treatment of erythema in rosacea in the absence of papules and pustules has not been evaluated. Rosacea is a common skin condition thought to be primarily an inflammatory disorder. Neutrophils, in particular, have been implicated in the inflammation associated with rosacea and mediate many of their effects through the release of reactive oxygen species. Many effective agents for rosacea, including topical azelaic acid have anti-inflammatory properties. Azelaic acid per se has multiple modes of action in rosacea, but an anti-inflammatory effect achieved by reducing reactive oxygen species appears to be the main pharmacological action. A possible mechanism of action for azelaic acid in the human epidermis includes its possibility to inhibit tyrosinase and of membrane-associated thioredoxin reductase enzymes, this enzyme is shown to regulate tyrosinase through a feedback mechanism involving electron transfer to intracellular thioredoxin, followed by a specific interaction between reduced thioredoxin and tyrosinase.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2505463
Curator's Comment: Azelaic acid is capable of crossing the blood-brain barrier: its concentration in the cerebrospinal fluid is normally in the range of 2-5% of the values in the serum.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P14679 Gene ID: 7299.0 Gene Symbol: TYR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2114832 |
2.73 mM [Ki] | ||
Target ID: CHEMBL2096978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2114832 |
125.0 mM [Ki] | ||
Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20967185 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | FINACEA Approved UseFINACEA® (azelaic acid) Gel, 15% is indicated for topical treatment of the inflammatory papules and pustules of mild to
moderate rosacea. Although some reduction of erythema which was present in patients with papules and pustules of
rosacea occurred in clinical studies, efficacy for treatment of erythema in rosacea in the absence of papules and pustules
has not been evaluated. Launch Date2002 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
112 ng/mL |
1 g single, topical dose: 1 g route of administration: Topical experiment type: SINGLE co-administered: |
AZELAIC ACID unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
136 ng/mL |
1 g 2 times / day steady-state, topical dose: 1 g route of administration: Topical experiment type: STEADY-STATE co-administered: |
AZELAIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
613 ng × h/mL |
1 g single, topical dose: 1 g route of administration: Topical experiment type: SINGLE co-administered: |
AZELAIC ACID unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
686 ng × h/mL |
1 g 2 times / day steady-state, topical dose: 1 g route of administration: Topical experiment type: STEADY-STATE co-administered: |
AZELAIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12 h |
1 g single, topical dose: 1 g route of administration: Topical experiment type: SINGLE co-administered: |
AZELAIC ACID unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Unraveling the patterns of subclinical pheomelanin-enriched facial hyperpigmentation: effect of depigmenting agents. | 2000 |
|
Combination azelaic acid therapy for acne vulgaris. | 2000 Aug |
|
["Cleansing, topical treatment, oral administration". Controlling acne]. | 2001 Jul 26 |
|
Comparison of combined azelaic acid cream plus oral minocycline with oral isotretinoin in severe acne. | 2001 Nov-Dec |
|
The management of rosacea. | 2002 |
|
Sensitive and accurate quantitation of monoepoxy fatty acids in thermoxidized oils by gas-liquid chromatography. | 2002 Dec 20 |
|
Total synthesis of (-)-minquartynoic acid: an anti-cancer, anti-HIV natural product. | 2002 Jul 25 |
|
Azelaic acid (20%) cream in the treatment of acne vulgaris. | 2002 Mar |
|
Fluid shear stress attenuates hydrogen peroxide-induced c-Jun NH2-terminal kinase activation via a glutathione reductase-mediated mechanism. | 2002 Oct 18 |
|
Burkholderia cepacia complex genomovars: utilization of carbon sources, susceptibility to antimicrobial agents and growth on selective media. | 2003 |
|
Topical treatment in acne: current status and future aspects. | 2003 |
|
Separation of homologues and isomers of linear alkylbenzenesulfonates by capillary electrophoresis with sodium dodecyl sulfate, carboxylic acids and bile salts. | 2003 Feb |
|
Urotropin azelate: a rather unwilling co-crystal. | 2003 Feb |
|
Management of acne. | 2003 Jan |
|
Gas chromatography-mass spectrometry profile of urinary organic acids of Wistar rats orally treated with ozonized unsaturated triglycerides and ozonized sunflower oil. | 2003 Jan 15 |
|
Interaction between a capacitor electrolyte and gamma-aluminum oxide studied by Fourier transform infrared spectroscopy. | 2003 Jun |
|
A comparison of 15% azelaic acid gel and 0.75% metronidazole gel in the topical treatment of papulopustular rosacea: results of a randomized trial. | 2003 Nov |
|
Acne and its management beyond the age of 35 years. | 2004 |
|
Photoelectron resonance capture ionization mass spectrometry: a soft ionization source for mass spectrometry of particle-phase organic compounds. | 2004 |
|
The subtypes of rosacea: implications for treatment. | 2004 Jan |
|
Maintenance therapy for acne vulgaris: the fine balance between efficacy, cutaneous tolerability, and adherence. | 2004 Jan-Feb |
|
Azelaic acid, a new treatment for rosacea. | 2004 Jun |
|
Conformationally constrained dipeptide surrogates with aromatic side-chains: synthesis of 4-aryl indolizidin-9-one amino acids by conjugate addition to a common alpha,omega-diaminoazelate enone intermediate. | 2004 Mar 5 |
|
Proposal to accommodate Burkholderia cepacia genomovar VI as Burkholderia dolosa sp. nov. | 2004 May |
|
Rosacea: where are we now? | 2004 May-Jun |
|
[Azelaic acid 15% gel in the treatment of acne vulgaris. Combined results of two double-blind clinical comparative studies]. | 2004 Oct |
|
Hyperpigmentation: an overview of the common afflictions. | 2004 Oct |
|
Comparison of 15% azelaic acid gel and 0.75% metronidazole gel for the topical treatment of papulopustular rosacea. | 2004 Oct |
|
Comparison of azelaic acid and anthralin for the therapy of patchy alopecia areata: a pilot study. | 2005 |
|
Aerosol products, mechanisms, and kinetics of heterogeneous reactions of ozone with oleic acid in pure and mixed particles. | 2005 |
|
Enhancement of the release of azelaic acid through the synthetic membranes by inclusion complex formation with hydroxypropyl-beta-cyclodextrin. | 2005 Apr 11 |
|
Considerations for treating acne in ethnic skin. | 2005 Aug |
|
Interventions for rosacea. | 2005 Jul 20 |
|
Acne vulgaris. | 2005 Jun |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
The pharmacologic therapy of rosacea: a paradigm shift in progress. | 2005 Mar |
|
The rigor of trials evaluating Rosacea treatments. | 2005 Mar |
|
Rosacea and its management: an overview. | 2005 May |
|
Cumulative irritation potential of metronidazole gel compared to azelaic acid gel after repeated applications to healthy skin. | 2005 Nov-Dec |
|
Face up to rosacea. | 2005 Sep |
|
Red facial rash with "granitos". | 2005 Sep |
|
The face and mind evaluation study: an examination of the efficacy of rosacea treatment using physician ratings and patients' self-reported quality of life. | 2005 Sep-Oct |
|
The use of topical azelaic acid for common skin disorders other than inflammatory rosacea. | 2006 Feb |
|
Case studies. | 2006 Feb |
|
A clinical overview of azelaic acid. | 2006 Feb |
|
The rationale for advancing the formulation of azelaic acid vehicles. | 2006 Feb |
|
The evolution of azelaic acid. | 2006 Feb |
|
Topical therapies for rosacea. | 2006 Jan |
|
Treatment of melasma. | 2006 May |
Patents
Sample Use Guides
Apply and gently massage into the affected areas on the face twice daily (morning and evening). Patients should be reassessed if no improvement is observed upon completing 12 weeks of therapy.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7640879
Using a clonogenic assay in vitro, it has been shown that exposure to azelaic acid (1-100 mM) for 24 hours has a dose-dependent effect on the survival of the colony-forming ability of murine (B16) and human (HMB2, and SK23) melanoma cells as compared with a non-melanotic non-tumoral Chinese hamster cell line (CHO). Both human cell lines were more sensitive to the diacid than the murine cells, and the HMB2 cells were more sensitive than the SK23 cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 20:09:05 GMT 2023
by
admin
on
Sat Dec 16 20:09:05 GMT 2023
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Record UNII |
0P4H8NH3UJ
|
Record Status |
Validated (UNII)
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Record Version |
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-
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27825-99-6
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NON-SPECIFIC STOICHIOMETRY | |||
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C010038
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DTXSID40889659
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17265-13-3
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0P4H8NH3UJ
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159815
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2117384
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241-298-4
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